F. Scott Fitzgerald faced numerous challenges throughout his writing career, including strict financial struggles, which often stemmed from his lifestyle and reliance on alcohol. His personal life, particularly his tumultuous marriage to Zelda Sayre, influenced his work and creativity. Additionally, Fitzgerald grappled with critical reception; his novels, especially "The Great Gatsby," initially did not achieve commercial success, leading to feelings of inadequacy. Ultimately, these difficulties shaped his literary legacy, highlighting the complexities of the American Dream.